The summers of 2015 and 2016 were the first time I travelled for a few months in a row. I had the absolute best time, despite being robbed on the first trip – and the second summer was perfect and I couldn’t wait to do it again. Sadly, I have had to work full time since, and I have still made room for several awesome trips, but I’ve been longing for the freedom of flexible travel – showing up in a city with no idea where I’m going to stay, scheduling a month to explore an unknown country – that kind of stuff.

After 2-ish years of blowing all my money in Toronto and admittedly being deeply irresponsible, I decided I needed to get my shit together and moved home to Nova Scotia to save money. I lived with my parents, then found the cheapest apartment ever and have been living as frugally as possible. And finally, I can afford to get back on the road!!!

When I started figuring out where I wanted to go and when, the only certainty was I needed to be in Greece for a week in June so I could do another yacht trip. Flexibility is KEY to finding cheap flights and I took full advantage of that. I started playing around with flights and realized I could possibly book a round the world trip….so I decided to see how cheap I could do it.
Approximately $2000 Canadian and nine tickets later, I have a route that sees me visiting 17 countries, 5 continents and having a whole bunch of adventures. Here’s how I did it!
I work at a travel agency, so I have all kinds of great systems that are awesome for finding flights. However, kiwi.com has been the absolute best tool ever for finding CHEAP flights. It has a tool that lets you search for ‘anywhere’ so I literally put in Halifax as the origin, found a cheap flight to Hawaii by hitting the anywhere button, and then hopped my way around the world using the anywhere button.
Kiwi is really cool because it pairs airlines together that you can’t normally book together. So instead of just showing you all the options from city to city with one airline, it tells you how to get their the very cheapest way. You might have to make long stops and they might be budget airlines, but it’s worth it to me! More on these layovers below.
Also, you can type in an entire country. When I was trying to figure out where to fly from India, I just typed in India as my origin – because I don’t care where I end my trip through the country! This opens up so many more options.

Here is the breakdown of how I did all these flights, with all pricing in Canadian dollars:
Halifax-Honolulu with Westjet $325
Honolulu-Sydney and Melbourne-Bali with Jetstar $469.73
Bali-Singapore with Air Asia $95
Singapore-Amritsar, India with Scoot $149
Kerala, India to Dubai with Indigo $136
Dubai to Sofia with Wizzair $175
Sofia to Athens with Ryanair $50
Istanbul to Tel Aviv with Pegasus $121
Cairo to Halifax via Athens and Dublin (24 hour stop there) $563
Grand total $2083!!! There are some legs where I’ll be travelling overland – between Greece and Turkey there is about 6 weeks of travel through the Balkans with no flights.

The other biggest money-saving tip I have is to fly carry-on only. I saved hundreds of dollars with these tickets because I don’t need to pay for luggage – which is never ever included on budget airlines. It is really important to make sure that you know how much your carryon weighs, because if you show up to the airport with something more than you paid for, they will charge you SO much more. On some of these flights I paid maybe $20 more to slightly increase the weight I’m allowed to take as a carryon, but if I had to check a bag, it would have been $100. Another post to come – but I am a die-hard carry-on only traveller.

And finally, my other biggest tip to see more of the world on trips like this – extend your layover! For example, on Kiwi when I searched flights from India to Greece, it had 5-6 hour layovers in Dubai and Bulgaria. I didn’t want to sit in Dubai airport for 5 hours, I want to see Dubai! And why not Bulgaria as well. So I checked if the flights out of Dubai and Bulgaria could be moved ahead to later in the day or a few days later, giving me time to actually see the cities – and they could. So rather than 24 hours of travel with really long layovers, I get 15 hours in Dubai to sightsee and two nights in the capital of Bulgaria. Short layovers are a great way to see where I want to spend more time in the future, and you can see a lot in a day in places like Dubai.
Another post to come with full details on my plans…..for now, let me know if you have any questions about using Kiwi or finding cheap flights!
I like your teal shorts
Wow! What an amazing booking and trip ahead! Good for you! Looking forward to following you along your travels! 🙂